How to Be a Sleazy Salesperson in 5 Easy Steps (Please Don’t)

Let’s face it—sales is hard. The targets are aggressive, your pipeline never feels full enough, and someone, somewhere, decided that “Always Be Closing” should be a personality type.

But here’s the truth: sleaze doesn’t sell.

You know the type—the overly eager rep who treats every discovery call like a hostage negotiation. And while we’re having a little fun with it here, that kind of sales behavior isn’t just annoying—it’s bad for business.

A Harvard Business Review study once found that 84% of B2B buyers begin the purchasing process with a referral. Why? Because they trust people who act like actual humans. Sales isn’t about relentless pitching—it’s about relationships.

But maybe you’re feeling a little rebellious. Maybe you're training for gold in the Greasy Sales Tactics™ Olympics. So, in the spirit of public service (and a good laugh), here’s your slightly sarcastic guide to becoming a world-class sleazy salesperson in just five easy steps.

1. Assume your pitch is more important than your client's time.

Got five minutes on the calendar? Perfect. Take fifteen. Nothing screams “you matter” like blowing past their hard stop, delivering a bloated intro, and asking questions you could’ve Googled in 30 seconds.

Bonus sleaze points if you make them feel like you did them a favor by showing up.

2. Don’t take “no” for an answer—or “yes,” for that matter.

The hallmark of sleaze is persistence. But not the good kind. If your prospect says, “Not now,” treat it like a challenge. Keep pushing. Maybe throw in a desperate “limited-time offer” or “you’d be crazy to walk away from this.”

Because nothing says “trust me with your business” like ignoring basic verbal cues and pretending urgency equals value.

3. Steamroll the “yes.”

Client says, “We love your service—we’ll come back when we’re ready.” Do you thank them and nurture the relationship? Of course not! Cue the 20-minute repitch. Toss in a little guilt. Maybe even end with: “Seems odd, but hey—it’s your choice. Good luck out there.”

Now that’s how you turn a referral into a cautionary tale.

4. Pivot hard—preferably into something completely unrelated.

They came for a refi? Perfect time to upsell them a wireless security system. Or solar panels. Or a yacht timeshare. Why stop at one offering when you can throw in the entire product catalog?

If your team is pivoting mid-call like this, it’s not cross-selling—it’s chaos.

5. Follow up like a caffeine-fueled stalker.

Call. Email. Text. DM. Fax. (Yes, fax—for the vintage charm.) If you’re not setting at least five calendar reminders per prospect, are you even trying? There’s persistence… and then there’s pestering.

Because nothing screams “I respect your boundaries” like a sixth LinkedIn message at 11 p.m.

Let’s Get Serious for a Second…

Sales is high-pressure, we get it. However, when customers feel hunted rather than helped, the damage is done. And here’s the kicker: You might not be the sleazy one, but is your team?

Hiring the right sales talent isn’t just about finding someone who can “close.” It’s about hiring professionals who understand trust, timing, and tact.

At Ascentria Search Partners, we specialize in connecting growth-minded companies with sales leaders who get it—people who sell with confidence, credibility, and emotional intelligence.

Our recruiters go beyond the resume to find people who align with your brand, your culture, and your long-term goals—so your next hire isn’t just effective today. They’re someone your customers want to work with again and again.

Because great salespeople don’t just drive revenue—they build reputations. Yours included.

One Last Thought (and Yes, This One’s Earnest)

If your sales team is skimming the sleazy end of the spectrum, don’t panic. There’s room for a reset—and we’re here to help.

Whether you’re scaling your team, replacing a miss-hire, or just ready to bring in someone who can sell without the cringe, Ascentria Search Partners is your go-to for high-impact, high-integrity talent.

Let’s talk. We promise not to pitch you a wireless security system.